methyl (2S,4S,5R,6R)-5-azido-6-[(1S,2R)-1,2-bis[(4-chlorobenzoyl)oxy]-3-hydroxypropyl]-4-(4-chlorobenzoyl)oxy-2-methoxyoxane-2-carboxylate | 1053260-72-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2S,4S,5R,6R)-5-azido-6-[(1S,2R)-1,2-bis[(4-chlorobenzoyl)oxy]-3-hydroxypropyl]-4-(4-chlorobenzoyl)oxy-2-methoxyoxane-2-carboxylate
• CAS: 1053260-72-2
• 化学式: C₃₂H₂₈Cl₃N₃O₁₁
• 分子量: 736.947
• InChiKey: JAKOEXUOULVZIS-UTRGJRIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  49
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  158
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl (methyl 4,7,8,9-tetra-O-acetyl-5-azido-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranosid)onate 、 methyl (2S,4S,5R,6R)-5-azido-6-[(1S,2R)-1,2-bis[(4-chlorobenzoyl)oxy]-3-hydroxypropyl]-4-(4-chlorobenzoyl)oxy-2-methoxyoxane-2-carboxylate 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 3 A molecular sieve 作用下， 以 乙腈 为溶剂， 以60%的产率得到
  参考文献：
  名称：

  The Thioglycoside and Glycosyl Phosphite of 5-Azido Sialic Acid: Excellent Donors for theα-Glycosylation of Primary Hydroxy Groups

  摘要：

  5-Azido sialyl donors with O-acetyl protecting groups are useful α-selective glycosylation reagents, especially for primary hydroxyl groups as acceptors. This is shown with a variety of reactions using 1 as a sialyl donor. It was also possible to synthesize NeuAcα(2→9)NeuAc as a thioglycoside donor for use in subsequent glycosylations.

  DOI：

  10.1002/1521-3773(20010803)40:15<2900::aid-anie2900>3.0.co;2-4
• 作为产物：
  描述：

  N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 在 吡啶 、 4-二甲氨基吡啶 、 甲烷磺酸 、 triflic azide 、 氢氟酸 、 copper(II) sulfate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 90.0h， 生成 methyl (2S,4S,5R,6R)-5-azido-6-[(1S,2R)-1,2-bis[(4-chlorobenzoyl)oxy]-3-hydroxypropyl]-4-(4-chlorobenzoyl)oxy-2-methoxyoxane-2-carboxylate
  参考文献：
  名称：

  The Thioglycoside and Glycosyl Phosphite of 5-Azido Sialic Acid: Excellent Donors for theα-Glycosylation of Primary Hydroxy Groups

  摘要：

  5-Azido sialyl donors with O-acetyl protecting groups are useful α-selective glycosylation reagents, especially for primary hydroxyl groups as acceptors. This is shown with a variety of reactions using 1 as a sialyl donor. It was also possible to synthesize NeuAcα(2→9)NeuAc as a thioglycoside donor for use in subsequent glycosylations.

  DOI：

  10.1002/1521-3773(20010803)40:15<2900::aid-anie2900>3.0.co;2-4

文献信息

• The Thioglycoside and Glycosyl Phosphite of 5-Azido Sialic Acid: Excellent Donors for theα-Glycosylation of Primary Hydroxy Groups
  作者：Chung-Shan Yu、Kenichi Niikura、Chun-Cheng Lin、Chi-Huey Wong

  DOI：10.1002/1521-3773(20010803)40:15<2900::aid-anie2900>3.0.co;2-4

  日期：2001.8.3

  5-Azido sialyl donors with O-acetyl protecting groups are useful α-selective glycosylation reagents, especially for primary hydroxyl groups as acceptors. This is shown with a variety of reactions using 1 as a sialyl donor. It was also possible to synthesize NeuAcα(2→9)NeuAc as a thioglycoside donor for use in subsequent glycosylations.